Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes

A highly enantio‐ and diastereoselective copper‐catalyzed three‐component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. The method utilizes a commercially available NHC ligand and copper source, operates at ambient...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2016-09, Vol.55 (39), p.11912-11916
Main Authors: Yeung, Kay, Ruscoe, Rebecca E., Rae, James, Pulis, Alexander P., Procter, David J.
Format: Article
Language:English
Subjects:
Ambient temperature
Amines
asymmetric catalysis
boron
Communication
Communications
Copper
Coupling
Enantiomers
Imines
multicomponent reactions
Stereoselectivity
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Summary:A highly enantio‐ and diastereoselective copper‐catalyzed three‐component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples readily available simple imines, allenes, and diboranes, and yields high‐value homoallylic amines that exhibit versatile amino, alkenyl, and boryl units. A copper‐catalyzed three‐component coupling affords homoallylic amines with adjacent stereocenters from achiral starting materials with high enantio‐ and diastereoselectivity. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples simple imines, allenes, and diboranes, and yields valuable homoallylic amines with versatile amino, alkenyl, and boryl units.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201606710